A person running.
No, not that one. Try again.
A right answer but not the one I meant, so keep it. A person with a diamond head.
Correct. A chair with a tall back.
No, not that one. Try again.
No, not that one. This chair looks like a lower-case letter h.
Not what I meant, but a right answer, so keep it. Now add the chair.
Again, no. Not that shape. This shape is like a lower case letter h or a chair with a tall back that bends near the top.
No, not that one.  Try again.
No, not that one. This shape is almost entirely flat on hte left side.

Outcome: unsuccessful
Speaker comments: Bot was a mess on this one, all over the place, and didn't listen to feedback.